Norhydrocodone

Norhydrocodone
Identifiers
Synonyms (5α)-3-Methoxy-4,5-epoxymorphinan-6-one
CAS Number 5083-62-5
PubChem (CID) 13001738
ChemSpider 32698944
UNII 18NB5F1JT4
Chemical and physical data
Formula C17H19NO3
Molar mass 285.34 g·mol−1
3D model (Jmol) Interactive image

Norhydrocodone is the major metabolite of the opioid analgesic hydrocodone.[1] It is formed from hydrocodone in the liver via N-demethylation predominantly by CYP3A4.[1] Unlike hydromorphone, a minor metabolite of hydrocodone, norhydrocodone is described as inactive.[2] However, norhydrocodone is actually an agonist of the μ-opioid receptor with similar potency to hydrocodone, but has been found to produce only minimal analgesia when administered peripherally to animals.[3] This is likely due to poor blood-brain-barrier and thus central nervous system penetration.[3]

See also

References

  1. 1 2 Shufeng Zhou (6 April 2016). Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism. CRC Press. pp. 164–. ISBN 978-1-4665-9788-4.
  2. Amitava Dasgupta; Loralie J. Langman (23 April 2012). Pharmacogenomics of Alcohol and Drugs of Abuse. CRC Press. pp. 175–. ISBN 978-1-4398-5611-6.
  3. 1 2 Navani, D. M.; Yoburn, B. C. (2013). "In Vivo Activity of Norhydrocodone: An Active Metabolite of Hydrocodone". Journal of Pharmacology and Experimental Therapeutics. 347 (2): 497–505. doi:10.1124/jpet.113.207548. ISSN 1521-0103.



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